Charles Arthur "Pretty Boy" Floyd was born in Adairsville, Georgia, on February 3, 1904. He was the fourth of eight children born to Walter Lee Floyd and Minnie (Echols). The family moved to Oklahoma in 1911 where they worked as tenant farmers.
His parents nicknamed him "Choc," and that was the name he was most commonly known by. No one who knew him called him "Pretty Boy". In fact, it is commonly accepted that he did not approve of that nickname. He attended school and completed the sixth grade, which at the time, was considered an adequate education.
In 1919, Floyd went off to harvest fields in Kansas and Oklahoma with a paid work crew. It was at this time that he met a class of individual that would change his perspective on work and success; the drifter and vagabond. These men told stories of easy money and fast living. This appealed to Floyd since his current occupation as a farmhand and laborer was difficult and didn't pay well.
He was first arrested in 1922 for stealing $3.50 from a post office. Although the amount stolen was minimal, robbing a government post office was a federal offense and. He got off only because witnesses failed to appear in court.
In 1924, Floyd married Ruby Hargraves. They had one son, Charles Dempsey Floyd. In the months following his marriage, he worked in the fields of neighboring cotton farms picking cotton. Within the year Floyd met John Hilderbrand, a thief who was hiding from the police. Hilderbrand persuaded Floyd to join him as he robbed food stores and service stations.
In September, 1925, Floyd, Hilderbrand and fellow criminal, Joe Hlavatry, were arrested for robbing the payroll of a St. Louis Kroger's store. All three men were convicted and Floyd was sentenced to five years in prison. During this time, Ruby divorced him. They would continue to live together off and on for the rest of his life.
When he was released from prison in 1929, he went to Kansas City, Missouri where he reunited with prison pal Alfred "Red" Lovett. Lovett helped Floyd acclimate to life on the outside by getting him a place to live and introducing him to people that could help him earn a living. Although organized crime was rampant in Kansas City, on the advice of Lovett, Floyd remained independent. It was in Kansas City that Floyd met and fell in love with rival outlaw, Wallace Ash's wife, Beulah "Juanita" Baird. Their relationship would continue on and off for the rest of his life.
In January, 1930 Floyd left Kansas City for Ohio with the Jim Bradley Gang. They planned to "hit" a number of prosperous banks in and around Toledo and Akron. Besides Jim Bradley, the gang included members Nathan King and Nellie Maxwell. The experienced limited success on their venture, until they were captured on March 8th in Akron, Ohio. In November of that year, Floyd was sentenced to fifteen years maximum at the Ohio State Penitentiary. He escaped while en route to the penitentiary at Columbus.
In 1931, an old friend from the hills, George Birdwell, joined Floyd and, between 1931 and 1932, Floyd and Birdwell held up more banks than anyone in Oklahoma's history.
On April 7, 1932 Floyd shot and killed Erv Kelley, a former McIntosh County, Oklahoma sheriff turned bounty hunter. Erv Kelley was attempting to ambush Floyd near Bixby, Oklahoma. The FBI believed that Floyd, along with associates Verne Miller and Adam Richetti, participated in the June 17, 1933 Kansas City Massacre. Four lawmen were killed during this bloody attempt to help fellow robber Frank Nash escape custody. Floyd denied to the very end that he had anything to do with the massacre and most historians agree that he probably wasn't there, but because of his notoriety, he is linked with the incident.
It is believed that Floyd joined the Dillinger Gang when they held up the Merchants National Bank in South Bend, Indiana on June 30, 1934. A cashier and the bank director both identified Floyd afterwards. Following the death of John Dillinger, Pretty Boy Floyd became "Public Enemy Number 1"on July 23, 1934.
Charles Arthur Floyd was shot and killed on October 22, 1934 by FBI and local law enforcement officers led by FBI agent Melvin Purvis in a cornfield or orchard near East Liverpool, Ohio.